Sodium Hydroxide → HCID 22403909, compound

HRID 259858Notes

Reaction equation

HRID 259858 reaction equation
C([O:4][C:5]1[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][C:8]([C:9]([NH:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:19][C:18]([CH3:29])=[CH:17][C:16]=3[CH3:30])=[O:10])=[CH:7][C:6]=1[CH:36]([CH3:38])[CH3:37])(=O)C.[OH-].[Na+]>CO>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:21]1[C:20]2[C:15](=[C:16]([CH3:30])[CH:17]=[C:18]([CH3:29])[CH:19]=2)[N:14]=[CH:13][C:12]=1[NH:11][C:9](=[O:10])[C:8]1[CH:7]=[C:6]([CH:36]([CH3:38])[CH3:37])[C:5]([OH:4])=[C:32]([CH:33]([CH3:35])[CH3:34])[CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22403912HCID 22403912, compound

Product 1

HCID 22403909HCID 22403909, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(4-acetoxy-3,5-diisopropylbenzamido)-4-(2-chlorophenyl)-6,8-dimethylquinoline (600 mg), methanol (40 ml) and 1N-sodium hydroxide (4 ml) was stirred at room temperature for 3 hours. After concentrating, the mixture was diluted with water and made acidic with 2N-hydrocloric acid. Thereafter, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was removed and the residue was recrystallized from acetone-isopropyl ether to give 4-(2-chlorophenyl)-3-(4-hydroxy-3,5-diisopropyl benzamido)-6,8-dimethylquinoline (494 mg, 89.5%) as colorless prisms.

Workup

  1. concentrationAfter concentrating
  2. additionthe mixture was diluted with water
  3. extractionThereafter, the mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customthe residue was recrystallized from acetone-isopropyl ether

Sources & evidence

ORD record
ord-c1ce0dd5e6f54447b3ef7e6877d7bacd
Source dataset
uspto-grants-1996_06
Patent number
US05523407

Reaction notes

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